Water → HCID 18428501, compound

HRID 1003474Notes

Reaction equation

HRID 1003474 reaction equation
[CH:1]([CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]1[CH:11]([CH3:12])[CH2:10][C:9](=[O:13])[NH:8]1)=[CH2:2].C[N+]1([O-])CC[O:26]CC1.CC(O)(C)C.[OH2:35]>CC(C)=O.O.O=[Os](=O)(=O)=O>[OH:35][CH:1]([CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]1[CH:11]([CH3:12])[CH2:10][C:9](=[O:13])[NH:8]1)[CH2:2][OH:26]

Participants

7

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 18428617HCID 18428617, compound

Product 1

HCID 18428501HCID 18428501, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirring solution of the compound from EXAMPLE 259 (3.3 mmol) in 80 mL of acetone:H2O (3:1) is added N-methylmorpholine N-oxide (0.64 g, 4.8 mmol) and 2.5% OsO4 in t-BuOH (3.4 mL, 3.4 mmol). After 18 h, 120 mL of H2O, 8 g of celite, and 1.6 g Na2S2O1 is added to the reaction. The reaction is filtered through a pad of wet celite. To the filtrate is added 200 mL of 1M KHSO4. The filtrate is extracted with 3×200 mL EtOAc. The combined organic layers are dried, filtered, and stripped. The residue is purified by chromatography to yield the title compound.

Workup

  1. filtrationThe reaction is filtered through a pad of wet celite
  2. additionTo the filtrate is added 200 mL of 1M KHSO4
  3. extractionThe filtrate is extracted with 3×200 mL EtOAc
  4. customThe combined organic layers are dried
  5. filtrationfiltered
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-b9c6c7e06b824aa09d78cdab5623aac1
Source dataset
uspto-grants-2000_04
Patent number
US06046211

Reaction notes

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